Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2- d ][1,4]oxazepin-5(3 H )ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence - Le Mans Université Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2017

Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2- d ][1,4]oxazepin-5(3 H )ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence

Résumé

The access to new oxazolo[3,2-d][1,4]oxazepin-5(3H)-ones starting from α-bromoamido alcohols and Michael acceptors under mild conditions is presented. This domino process proved to be chemo-, regio-, and stereoselective and allows the formation of a large diversity of highly functional 7-membered rings in good yields up to 95%. The complete shift of the regioselectivity of the intermediate enolate from a C–C to a C–O bond formation, contrary to the already known alkylations of such ambident nucleophiles, is mostly triggered by steric effects. The last step of the sequence was modeled by DFT giving some important insights for this C–C vs C–O bond shift.
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Dates et versions

hal-01912420 , version 1 (05-11-2018)

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Abderrahman El Bouakher, Jordan Tasserie, Ronan Le Goff, Jérôme Lhoste, Arnaud Martel, et al.. Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2- d ][1,4]oxazepin-5(3 H )ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence. Journal of Organic Chemistry, 2017, 82 (11), pp.5798-5809. ⟨10.1021/acs.joc.7b00629⟩. ⟨hal-01912420⟩
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